data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 N8 O1.50 Zn' _chemical_formula_weight 356.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.247(3) _cell_length_b 14.165(4) _cell_length_c 10.703(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.063(8) _cell_angle_gamma 90.00 _cell_volume 1407.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7345 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.50 _exptl_crystal_description sheet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 1.765 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6869 _exptl_absorpt_correction_T_max 0.7534 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13931 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2760 _reflns_number_gt 2309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.4194P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2760 _refine_ls_number_parameters 215 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0737 _refine_ls_wR_factor_gt 0.0706 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.5832(7) 0.5470(4) 0.9419(5) 0.0947(17) Uani 0.50 1 d PD . . H2A H 0.647(6) 0.511(6) 0.932(5) 0.142 Uiso 0.50 1 d PD . . H2B H 0.508(4) 0.557(5) 0.863(3) 0.142 Uiso 0.50 1 d PD . . Zn1 Zn 0.35712(2) 0.448794(16) 0.53856(2) 0.02695(10) Uani 1 1 d . . . O1 O 0.35051(17) 0.55286(10) 0.67779(16) 0.0350(4) Uani 1 1 d . . . N1 N 0.26306(19) 0.37947(12) 0.33626(17) 0.0280(4) Uani 1 1 d . . . N2 N 0.1138(3) 0.30944(15) 0.0705(2) 0.0485(5) Uani 1 1 d . . . N3 N 0.16440(18) 0.51668(12) 0.43293(17) 0.0247(4) Uani 1 1 d . . . N4 N 0.13262(18) 0.59309(12) 0.49498(17) 0.0278(4) Uani 1 1 d . . . N5 N 0.18399(18) 0.83472(12) 0.85378(17) 0.0280(4) Uani 1 1 d . . . N6 N 0.5700(2) 0.43112(14) 0.6068(2) 0.0356(4) Uani 1 1 d U . . N7 N 0.6501(2) 0.41887(14) 0.7256(2) 0.0374(4) Uani 1 1 d U . . N8 N 0.7335(3) 0.40730(19) 0.8378(2) 0.0615(7) Uani 1 1 d . . . C1 C 0.3182(3) 0.31186(16) 0.2871(2) 0.0359(5) Uani 1 1 d . . . H1 H 0.4084 0.2870 0.3425 0.043 Uiso 1 1 calc R . . C2 C 0.2428(3) 0.27786(17) 0.1540(3) 0.0452(6) Uani 1 1 d . . . H2 H 0.2848 0.2309 0.1223 0.054 Uiso 1 1 calc R . . C3 C 0.0595(3) 0.37782(17) 0.1204(2) 0.0405(6) Uani 1 1 d . . . H3 H -0.0310 0.4018 0.0644 0.049 Uiso 1 1 calc R . . C4 C 0.1325(2) 0.41459(15) 0.2524(2) 0.0271(4) Uani 1 1 d . . . C5 C 0.0787(2) 0.49392(14) 0.3084(2) 0.0269(5) Uani 1 1 d . . . C6 C -0.0593(3) 0.54382(16) 0.2240(3) 0.0416(6) Uani 1 1 d . . . H6A H -0.1020 0.5658 0.2831 0.062 Uiso 1 1 calc R . . H6B H -0.1243 0.5011 0.1568 0.062 Uiso 1 1 calc R . . H6C H -0.0403 0.5966 0.1780 0.062 Uiso 1 1 calc R . . C7 C 0.2384(2) 0.60368(14) 0.6204(2) 0.0268(5) Uani 1 1 d . . . C8 C 0.2188(2) 0.68467(14) 0.7006(2) 0.0266(4) Uani 1 1 d . . . C9 C 0.2837(3) 0.68386(17) 0.8433(2) 0.0411(6) Uani 1 1 d . . . H9 H 0.3411 0.6332 0.8907 0.049 Uiso 1 1 calc RD . . C10 C 0.2624(3) 0.75889(17) 0.9143(2) 0.0399(6) Uani 1 1 d . . . H10 H 0.3053 0.7566 1.0101 0.048 Uiso 1 1 calc R . . C11 C 0.1234(2) 0.83541(16) 0.7153(2) 0.0367(5) Uani 1 1 d . . . H11 H 0.0693 0.8879 0.6703 0.044 Uiso 1 1 calc R . . C12 C 0.1369(2) 0.76311(16) 0.6371(2) 0.0357(5) Uani 1 1 d . . . H12 H 0.0911 0.7666 0.5414 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.090(4) 0.105(4) 0.063(3) -0.024(3) 0.007(3) 0.020(3) Zn1 0.02627(16) 0.02593(15) 0.02445(15) -0.00034(9) 0.00668(11) 0.00324(9) O1 0.0370(9) 0.0328(8) 0.0284(8) -0.0050(6) 0.0073(7) 0.0111(7) N1 0.0337(10) 0.0254(9) 0.0254(9) -0.0012(7) 0.0129(8) -0.0024(7) N2 0.0683(15) 0.0438(12) 0.0297(11) -0.0095(9) 0.0170(11) -0.0030(11) N3 0.0279(9) 0.0240(9) 0.0234(9) -0.0005(7) 0.0120(8) -0.0008(7) N4 0.0308(10) 0.0255(9) 0.0279(9) -0.0021(7) 0.0132(8) 0.0031(7) N5 0.0303(9) 0.0262(9) 0.0270(9) -0.0027(7) 0.0118(8) 0.0012(7) N6 0.0251(10) 0.0447(11) 0.0351(11) 0.0050(9) 0.0110(8) 0.0014(8) N7 0.0308(10) 0.0378(10) 0.0427(12) 0.0074(9) 0.0148(10) -0.0004(8) N8 0.0516(15) 0.0752(17) 0.0412(13) 0.0178(12) 0.0035(12) 0.0000(13) C1 0.0441(14) 0.0306(12) 0.0355(12) -0.0012(10) 0.0192(11) 0.0036(10) C2 0.0678(18) 0.0342(13) 0.0413(14) -0.0064(11) 0.0306(14) 0.0036(12) C3 0.0435(14) 0.0427(13) 0.0278(12) -0.0039(11) 0.0079(11) -0.0017(11) C4 0.0299(11) 0.0271(10) 0.0231(10) 0.0007(8) 0.0100(9) -0.0043(9) C5 0.0251(11) 0.0295(11) 0.0250(11) 0.0018(9) 0.0095(9) -0.0027(9) C6 0.0340(13) 0.0460(15) 0.0353(13) -0.0003(11) 0.0055(11) 0.0059(10) C7 0.0317(12) 0.0249(11) 0.0264(11) 0.0005(9) 0.0148(10) -0.0014(9) C8 0.0280(11) 0.0247(10) 0.0283(10) -0.0012(9) 0.0130(9) 0.0002(8) C9 0.0491(15) 0.0354(13) 0.0320(12) 0.0016(10) 0.0105(11) 0.0166(11) C10 0.0484(15) 0.0412(13) 0.0225(11) -0.0034(10) 0.0077(10) 0.0126(11) C11 0.0431(14) 0.0340(12) 0.0304(12) 0.0031(10) 0.0132(10) 0.0125(10) C12 0.0413(13) 0.0376(13) 0.0245(11) -0.0005(10) 0.0105(10) 0.0093(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 H2A 0.87(2) . ? O2 H2B 0.88(2) . ? Zn1 N6 2.0009(19) . ? Zn1 N3 2.0521(17) . ? Zn1 O1 2.1176(15) . ? Zn1 N5 2.1277(17) 2_546 ? Zn1 N1 2.1939(17) . ? O1 C7 1.271(3) . ? N1 C1 1.329(3) . ? N1 C4 1.351(3) . ? N2 C2 1.321(3) . ? N2 C3 1.336(3) . ? N3 C5 1.288(3) . ? N3 N4 1.379(3) . ? N4 C7 1.329(3) . ? N5 C10 1.333(3) . ? N5 C11 1.342(3) . ? N5 Zn1 2.1277(17) 2_556 ? N6 N7 1.198(3) . ? N7 N8 1.154(3) . ? C1 C2 1.387(3) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.390(3) . ? C3 H3 0.9300 . ? C4 C5 1.485(3) . ? C5 C6 1.494(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.496(3) . ? C8 C9 1.383(3) . ? C8 C12 1.385(3) . ? C9 C10 1.376(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.366(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H2A O2 H2B 112(3) . . ? N6 Zn1 N3 154.89(7) . . ? N6 Zn1 O1 100.67(7) . . ? N3 Zn1 O1 75.60(6) . . ? N6 Zn1 N5 98.20(7) . 2_546 ? N3 Zn1 N5 106.80(7) . 2_546 ? O1 Zn1 N5 94.29(7) . 2_546 ? N6 Zn1 N1 105.03(7) . . ? N3 Zn1 N1 75.41(7) . . ? O1 Zn1 N1 150.98(6) . . ? N5 Zn1 N1 95.14(7) 2_546 . ? C7 O1 Zn1 110.23(13) . . ? C1 N1 C4 118.02(19) . . ? C1 N1 Zn1 129.12(15) . . ? C4 N1 Zn1 112.83(13) . . ? C2 N2 C3 116.2(2) . . ? C5 N3 N4 119.86(17) . . ? C5 N3 Zn1 121.87(15) . . ? N4 N3 Zn1 118.09(12) . . ? C7 N4 N3 108.47(16) . . ? C10 N5 C11 116.34(19) . . ? C10 N5 Zn1 124.45(14) . 2_556 ? C11 N5 Zn1 119.15(14) . 2_556 ? N7 N6 Zn1 123.81(16) . . ? N8 N7 N6 176.3(3) . . ? N1 C1 C2 120.8(2) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? N2 C2 C1 122.7(2) . . ? N2 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? N2 C3 C4 122.8(2) . . ? N2 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? N1 C4 C3 119.5(2) . . ? N1 C4 C5 116.31(17) . . ? C3 C4 C5 124.2(2) . . ? N3 C5 C4 113.55(18) . . ? N3 C5 C6 124.3(2) . . ? C4 C5 C6 122.15(18) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O1 C7 N4 127.40(19) . . ? O1 C7 C8 118.04(18) . . ? N4 C7 C8 114.56(18) . . ? C9 C8 C12 117.2(2) . . ? C9 C8 C7 120.56(19) . . ? C12 C8 C7 122.29(19) . . ? C10 C9 C8 119.2(2) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? N5 C10 C9 123.9(2) . . ? N5 C10 H10 118.0 . . ? C9 C10 H10 118.0 . . ? N5 C11 C12 123.5(2) . . ? N5 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C11 C12 C8 119.9(2) . . ? C11 C12 H12 120.1 . . ? C8 C12 H12 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N6 Zn1 O1 C7 150.80(15) . . . . ? N3 Zn1 O1 C7 -3.75(14) . . . . ? N5 Zn1 O1 C7 -110.01(14) 2_546 . . . ? N1 Zn1 O1 C7 -1.3(2) . . . . ? N6 Zn1 N1 C1 23.0(2) . . . . ? N3 Zn1 N1 C1 177.0(2) . . . . ? O1 Zn1 N1 C1 174.55(16) . . . . ? N5 Zn1 N1 C1 -76.97(19) 2_546 . . . ? N6 Zn1 N1 C4 -155.09(14) . . . . ? N3 Zn1 N1 C4 -1.08(14) . . . . ? O1 Zn1 N1 C4 -3.5(2) . . . . ? N5 Zn1 N1 C4 104.97(14) 2_546 . . . ? N6 Zn1 N3 C5 94.5(2) . . . . ? O1 Zn1 N3 C5 178.92(17) . . . . ? N5 Zn1 N3 C5 -90.90(17) 2_546 . . . ? N1 Zn1 N3 C5 0.13(16) . . . . ? N6 Zn1 N3 N4 -80.7(2) . . . . ? O1 Zn1 N3 N4 3.74(14) . . . . ? N5 Zn1 N3 N4 93.92(15) 2_546 . . . ? N1 Zn1 N3 N4 -175.05(16) . . . . ? C5 N3 N4 C7 -178.21(18) . . . . ? Zn1 N3 N4 C7 -2.9(2) . . . . ? N3 Zn1 N6 N7 127.7(2) . . . . ? O1 Zn1 N6 N7 48.9(2) . . . . ? N5 Zn1 N6 N7 -47.1(2) 2_546 . . . ? N1 Zn1 N6 N7 -144.70(19) . . . . ? Zn1 N6 N7 N8 -175(4) . . . . ? C4 N1 C1 C2 -0.7(3) . . . . ? Zn1 N1 C1 C2 -178.68(17) . . . . ? C3 N2 C2 C1 1.0(4) . . . . ? N1 C1 C2 N2 -0.6(4) . . . . ? C2 N2 C3 C4 -0.1(4) . . . . ? C1 N1 C4 C3 1.5(3) . . . . ? Zn1 N1 C4 C3 179.83(16) . . . . ? C1 N1 C4 C5 -176.48(19) . . . . ? Zn1 N1 C4 C5 1.8(2) . . . . ? N2 C3 C4 N1 -1.2(3) . . . . ? N2 C3 C4 C5 176.7(2) . . . . ? N4 N3 C5 C4 175.85(17) . . . . ? Zn1 N3 C5 C4 0.8(2) . . . . ? N4 N3 C5 C6 -1.7(3) . . . . ? Zn1 N3 C5 C6 -176.84(16) . . . . ? N1 C4 C5 N3 -1.7(3) . . . . ? C3 C4 C5 N3 -179.7(2) . . . . ? N1 C4 C5 C6 175.92(19) . . . . ? C3 C4 C5 C6 -2.0(3) . . . . ? Zn1 O1 C7 N4 3.9(3) . . . . ? Zn1 O1 C7 C8 -176.85(14) . . . . ? N3 N4 C7 O1 -0.9(3) . . . . ? N3 N4 C7 C8 179.86(16) . . . . ? O1 C7 C8 C9 -24.7(3) . . . . ? N4 C7 C8 C9 154.6(2) . . . . ? O1 C7 C8 C12 155.0(2) . . . . ? N4 C7 C8 C12 -25.7(3) . . . . ? C12 C8 C9 C10 1.0(4) . . . . ? C7 C8 C9 C10 -179.3(2) . . . . ? C11 N5 C10 C9 0.2(4) . . . . ? Zn1 N5 C10 C9 177.41(19) 2_556 . . . ? C8 C9 C10 N5 -1.3(4) . . . . ? C10 N5 C11 C12 1.0(3) . . . . ? Zn1 N5 C11 C12 -176.30(18) 2_556 . . . ? N5 C11 C12 C8 -1.3(4) . . . . ? C9 C8 C12 C11 0.2(3) . . . . ? C7 C8 C12 C11 -179.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A N8 0.87(2) 2.17(3) 2.997(6) 158(6) . O2 H2A N7 0.87(2) 2.58(4) 3.236(5) 133(4) . O2 H2B O1 0.88(2) 1.96(2) 2.824(5) 168(5) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.484 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.060